Sodium cyanoborohydride → HCID 17872261, compound

HRID 1386070Notes

Reaction equation

HRID 1386070 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:14]([C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[C:17]=1[CH:18]=O)[CH3:15].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:16]([CH2:14][CH3:15])[C:17]=1[CH2:18][NH:1][C:2]1[C:3]2[N:4]([C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH3:25]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 22672632HCID 22672632, compound

Product 1

HCID 17872261HCID 17872261, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 8-amino-2,3,6-trimethylimidazo[1,2-a]pyridine (0.5 g, 2.8 mmol), 2,6-diethylbenzaldehyde (0.7 g, 4.3 mmol) and zinc(II)chloride (0.44 g, 3 mmol) in 50 ml methanol was treated with sodium cyanoborohydride (0.19 g, 3 mmol) and then refluxed for 20 h. The methanol was evaporated under reduced pressure and the residue was dissolved in dichloromethylene and water. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel with dichloromethylene first and then dichloromethylene:ethylacetate (1:1) which yielded 0.42 g of the title compound.

Workup

  1. temperaturerefluxed for 20 h
  2. customThe methanol was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethylene
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on silica gel with dichloromethylene first

Sources & evidence

ORD record
ord-f6d2bd4e985f4d658fd6b9b2ca12a52f
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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